Bovine Metabolome Database: Showing metabocard for PA(16:0/16:0) (BMDB0000674)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:44 UTC

Update Date

2020-05-21 16:28:42 UTC

BMDB ID

BMDB0000674

Secondary Accession Numbers

BMDB00674

Metabolite Identification

Common Name

PA(16:0/16:0)

Description

PA(16:0/16:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Dipalmitoyl-3-sn-phosphatidic acid	ChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphate	ChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid	ChEBI
Dipalmitoyl phosphatidic acid	ChEBI
PA(32:0)	ChEBI
Phosphatidic acid(16:0/16:0)	ChEBI
Phosphatidic acid(32:0)	ChEBI
1,2-Dipalmitoyl-3-sn-phosphatidate	Generator
Dipalmitoyl phosphatidate	Generator
Phosphatidate(16:0/16:0)	Generator
Phosphatidate(32:0)	Generator
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate	HMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid	HMDB
1,2-Dihexadecanoyl-rac-phosphatidic acid	HMDB
1,2-Dipalmitoyl-sn-glycerol 3-phosphate	HMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphorate	HMDB
Dipalmitoyl-L-a-phosphatidate	HMDB
Dipalmitoyl-L-a-phosphatidic acid	HMDB
Dipalmitoyl-L-alpha-phosphatidate	HMDB
Dipalmitoyl-L-alpha-phosphatidic acid	HMDB
Dipalmitoylphosphatidate	HMDB
Dipalmitoylphosphatidic acid	HMDB
L-a-Dipalmitoyl-phosphatidate	HMDB
L-a-Dipalmitoyl-phosphatidic acid	HMDB
L-a-Dipalmitoylphosphatidate	HMDB
L-a-Dipalmitoylphosphatidic acid	HMDB
L-alpha-Dipalmitoyl-phosphatidate	HMDB
L-alpha-Dipalmitoyl-phosphatidic acid	HMDB
L-alpha-Dipalmitoylphosphatidate	HMDB
L-alpha-Dipalmitoylphosphatidic acid	HMDB
Dipalmitoylphosphatidic acid, calcium salt	HMDB
Dipalmitoylphosphatidic acid, ammonium salt	HMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphate	HMDB
Dipalmitoylphosphatidic acid, sodium salt	HMDB
Dipalmitoylphosphatidic acid, (+-)-isomer	HMDB
Dipalmitoylphosphatidic acid, (R)-isomer	HMDB

Chemical Formula

C₃₅H₆₉O₈P

Average Molecular Weight

648.903

Monoisotopic Molecular Weight

648.47300618

IUPAC Name

[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid

Traditional Name

dipalmitoyl

CAS Registry Number

7091-44-3

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1

InChI Key

PORPENFLTBBHSG-MGBGTMOVSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate (CHEBI:73246 )
Diacylglycerophosphates (LMGP10010027 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Intracellular membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	161 - 165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.66	ALOGPS
logP	11.88	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	178.57 m³·mol⁻¹	ChemAxon
Polarizability	80.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9236341000-d0296e5b3dd53599a39d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0002-0000009000-b3b708036c56c15fec89	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1492100000-5624ed03f664b67f79ec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1490000000-1ba8a217ef22599ee07c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0002009000-7bdcaa7752c2e2970fdf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000900000-42187062de8aa3a7fcef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a71-4092103000-08a70ad05021be172e3b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-dc7f569f98cd450257d0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f628227e9a0ceffbeaf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000009000-8e723670c2d6da7d1500	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000099000-cef7e1d91751b702106e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-0000946000-9592d132939363ae4ad4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-5d6932d42201ac99e40a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052e-1166109000-3a40d8a06827026e1331	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1191101000-55ca7d5b11a7d0030aea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0000009000-6c5d51790d44b8f28697	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-0000059000-f0c15a320524af660ac4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-0006093000-7e3d155745f467b43ae7	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Intracellular membrane
Membrane

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000674

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022175

KNApSAcK ID

Not Available

Chemspider ID

393518

KEGG Compound ID

C00416

BioCyc ID

CPD0-1422

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5644

PubChem Compound

446066

PDB ID

Not Available

ChEBI ID

73246

References

Synthesis Reference

Ando, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya. Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho (2001), 8 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Lipid transport and metabolism
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis.
Gene Name:: PLD2
Uniprot ID:: Q0V8L6
Molecular weight:: 105766.0

Reactions

PA(16:0/16:0) → PE(16:0/16:0)	details

Enzyme Details

2. Diacylglycerol kinase alpha

General function:: Involved in calcium ion binding
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity.
Gene Name:: DGKA
Uniprot ID:: A0JN54
Molecular weight:: 82672.0

Reactions

DG(16:0/16:0/0:0) → PA(16:0/16:0)	details
DG(16:0/16:0/0:0) + Adenosine triphosphate → PA(16:0/16:0) + ADP	details

Enzyme Details

3. Lipin 1

General function:: Not Available
Specific function:: Not Available
Gene Name:: LPIN1
Uniprot ID:: E1BPE8
Molecular weight:: 102857.0

Reactions

PA(16:0/16:0) + Water → DG(16:0/16:0/0:0) + Hydrogen phosphate	details

Enzyme Details

4. 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha

General function:: Not Available
Specific function:: Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:: AGPAT1
Uniprot ID:: Q95JH2
Molecular weight:: 32005.0

Reactions

LPA(16:0/0:0) + Palmityl-CoA → Coenzyme A + PA(16:0/16:0)	details
LPA(16:0/0:0) → PA(16:0/16:0)	details
Palmityl-CoA + LPA(16:0/0:0) → PA(16:0/16:0) + Coenzyme A	details

Enzyme Details

5. 1-acyl-sn-glycerol-3-phosphate acyltransferase delta

General function:: Not Available
Specific function:: Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
Gene Name:: AGPAT4
Uniprot ID:: Q5E9R2
Molecular weight:: 43907.0

Reactions

LPA(16:0/0:0) + Palmityl-CoA → PA(16:0/16:0) + Coenzyme A	details

Enzyme Details

6. Phospholipid phosphatase 2

General function:: Not Available
Specific function:: Magnesium-independent phospholipid phosphatase that catalyzes the dephosphorylation of a variety of glycerolipid and sphingolipid phosphate esters including phosphatidate/PA, lysophosphatidate/LPA, sphingosine 1-phosphate/S1P and ceramide 1-phosphate/C1P. Has no apparent extracellular phosphatase activity and therefore most probably acts intracellularly. Also acts on N-oleoyl ethanolamine phosphate/N-(9Z-octadecenoyl)-ethanolamine phosphate, a potential physiological compound. Through dephosphorylation of these bioactive lipid mediators produces new bioactive compounds and may regulate signal transduction in different cellular processes (By similarity). Indirectly regulates, for instance, cell cycle G1/S phase transition through its phospholipid phosphatase activity (By similarity).
Gene Name:: PLPP2
Uniprot ID:: Q2HJ61
Molecular weight:: 32328.0

Reactions

PA(16:0/16:0) → DG(16:0/16:0/0:0) + Hydrogen phosphate	details

Showing metabocard for PA(16:0/16:0) (BMDB0000674)

Structure for BMDB0000674 (PA(16:0/16:0))

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions